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His Company Does $2.5m Per Employee Hauling Gravel For Uncle Sam

Inspired by the Jonah Hill movie "War Dogs," this founder built a successful government contracting firm that moves boulders instead of bombs.

Apple is famous for having one of the most financially productive workforces of any major tech company. With net sales of $394B and a staff of 164,000, they generated ~$2.4 million per employee in 2022.

Well, Dan Crowley's dump trucks topped that...

Crowley is a Hampton member, and founder of Crowley Holdings, which hauls sand and gravel for the US government.

With a team of six employees, and $10-$15 million per year revenue, he sneaks in just ahead of Apple at $2.5 million per head. A perfect example of how there really are great opportunities out there in the world of sweaty startups.

He also runs two other companies – one in trucking, one in real estate – which add another $5 million per year to the top line.

In today's interview, he takes us inside all three to explain how they work, the keys to their success (keep an eye out for the brilliant tax move that finances his trucks), and the tools and resources that have been crucial for him along the way.



Hello! Who are you and what business did you start?

My name is Daniel Crowley, and I guess I would describe myself as a serial entrepreneur. I’m originally from Massachusetts. I went to college in New Orleans and have stayed ever since. I now live here with my fiancé and dog.

I have three main businesses:

  • Crowley Holdings (government contracting)
  • Crowley Hauling (own and operate six dump trucks)
  • Crowley Properties (co-own and operate 24 short-term rental properties).

I couldn’t think of a good brand name so I just went with my last name: Crowley 🙂. 

I spend the majority of my time with Crowley Holdings, which I started in 2017. We do $10-15 million in annual revenue. It’s a government contracting business; we supply sand and gravel, as well as perform civil projects, for the government. 

I got the idea from the movie “War Dogs” and thought, "Man, I can do that!" But I didn't want to supply arms and munitions. So we started with sand and gravel — eventually, we won a contract and built the business up from there. 

In 2019, we won the largest rock delivery contract in Missouri state history:  roughly $23 million to deliver 550,000 tons of shot rock (about 30,000 dump truck loads). We had 100 or so dump trucks running all day, every day for about six months to repair three levee breaches.

Some of my other businesses include: 

  • Bulk Aggregate Supply: With this company, I’m hoping to combine my expertise in aggregate supply and delivery with the private sector. It’s in the works, with more to come soon.
  • Crowley Productions: I serve as executive producer on four small-budget movies hopefully coming to your screen soon

Between all businesses, we generate $15-20 million in revenue annually. 

I’m also a crypto/NFT, pre-seed, and seed investor, and one day I’d like to start an airline. (Hit me up if you want to start an airline, too.)

Over the years, I’ve taken to heart the motto from Richard Branson: “Screw it, just do it.” There are a million different ways to make money — and in my experience, it doesn’t have to be that hard. You just have to get out there and do it.

What's your backstory and how did you come up with these ideas?

For Crowley Holdings, the idea started after listening to this podcast on NPR, probably when it aired back in 2015. 

It was the story of two 20-somethings who ended up winning a ton of federal contracts. The story eventually became the movie “War Dogs” in 2016. 

One part of the story stuck out to me specifically.

One of the first contracts they won was supplying 50,000 gallons of propane — just by playing middle man and brokering the contract. They famously went on to win tens and, ultimately, hundreds of millions of dollars in contracts. They also did some illegal things that wound up getting them both in trouble with the law. 

I wasn’t drawn to the arms and munitions aspect — or, of course, doing anything illegal. But I remember thinking: "I could do what they are doing. Why can't I supply propane to the Air Force?"

Eventually, I started poking around the website, which is where the government posts RFQs (requests for quotes). Anything you can think of is on this website: RFQs for 100,000 rolls of toilet paper, 5,000 cardboard boxes, 20,000 slices of American cheese, bazookas, tanks, gravel…everything.

I submitted bids for a number of random items (cardboard boxes, leather jackets for the Air Force, etc.) before zeroing in on gravel. 

Eventually, we won our first contract. Since then, we’ve grown to bring in roughly $10-15 million a year in revenue with a team of six. 

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For Crowley Hauling, a lot of what we do involves dump trucks, so I had a good sense of how things worked. Founding the company felt like a natural way to diversify — an example of “Screw it, just do it!”

Over time, we’ve slowly built up to six dump trucks. I suspect we will get to 10+ over the next year or so.

A few of the trucks from Crowley's fleet

If you're smart about how you finance them, trucks like these can be used to offset taxes on other income (more on that below)

My final business, Crowley Properties, is an umbrella company that represents my ownership in each of the short-term rental properties I co-own in New Orleans and Tampa. 

There wasn’t really any “ah-ha” moment. I spotted the Airbnb opportunity and acted on it. This area still has a ton of opportunity.

Our business model is to create amazing common areas and outdoor spaces. This strategy has worked very well in both New Orleans and Tampa. I think it will work in most cities, and we plan on finding out! Here are a few pictures and links to a few of our properties:

Our villas in New OrleansIf you're going to run STRs, try to craft amazing outdoor and common areas. That's what captivates prospective guests and gets them excited to stay, Crowley says.

Historic home in New Orleans

"Pictures are what books a place," Crowley says. "Everything should be perfect in the pictures, otherwise retake them."

Tropical oasis in New Orleans 

Another great outdoor space designed to get visitors excited

Trendy seven-bedroom home in Tampa 

There's still lots of opportunity in the Tampa area for real estate investors willing to put in sweat equity, Crowley says.

Take us through the process of building the first version of your products.

For Crowley Holdings, the initial goal was to get our first sale. To start, I randomly submitted bids for government RFQs. I think I first submitted a contract for 10,000 cardboard boxes and then a contract for 500 leather jackets for the Air Force. I basically called around to get prices for whatever product the RFQ called for then marked it up and submitted it to the government.

Eventually, I zeroed in on aggregate. I submitted a bid for a contract for roughly 700 tons of limestone for an Air Force Base in Belle Chasse, LA. We didn’t win that one, but we started submitting more and more aggregate bids. 

Eventually, we won our first one in 2017. That’s when Ihad my “oh shit” moment: I realized I actually had to deliver 2,500 tons of graded aggregate base for the U.S. National Park Service in the Carolina Sandhills. 

“Damn, do I need to fly out there?” “What if something goes wrong?” “Should I be on site to manage the deliveries?” These were just a few of the immediate thoughts that came to my mind. The project went smoothly, and a business was born! 

Since then, we’ve slowly built up to 6-7 employees. Our next venture is trying to break into heavy civil construction work. We will do work for the U.S. Army Corps of Engineers to rebuild levees and other earthwork — definitely moving up to the big leagues. To start, these will be $5-10 million per project, but ultimately, I think we can get to $50-100 million revenue per year.

For Crowley Haulings, the idea formed after I spoke with someone who owned dump trucks. He connected me with a sales rep, and I eventually negotiated and bought my first truck in mid-2020:

  • I paid roughly $180,000
  • Financed 100% of the truck
  • Over a five-year payback period 
  • At a 5.5% interest rate

One huge benefit to buying dump trucks is that you can finance 100% of the truck and also depreciate 100% of the truck in the first year. 

As long as you have a good infrastructure — and can keep the trucks busy and profitable — you can just match each year with how well you are doing in your other businesses to offset income taxes. 

This is a good case study on how depreciation for tax purposes helps spur job growth. If you are looking at $200,000-$1 million in income, then you can just buy one to five dump trucks that year and depreciate them 100%. There is definitely risk here of course, but in theory, it could work that way.

For Crowley Properties, I started in 2012 with a business partner of mine (we still work together) by flipping a house in New Orleans. We bought our first house for $72,000, put sweat equity and about $50-60,000 into it, and sold it for $180,000. I think we ended up netting about $35-40,000 on it. But that was our first deal, and it worked! 

We went on to flip five more houses. Eventually, we started holding our properties and renting them out. That decision led us to where we are now.

Describe the process of launching the business.

With all of my businesses and ventures, one process is constant: going through the reps. Once you go through the process once, you then adjust  and it gets easier. Completing the second flip is much easier than the first. Buying and operating the second dump truck is much easier than the first. Winning the second government contract is way easier than the first.

So I would say my process is: just let it rip! Get it out there and tweak.

Since launch, what has worked to attract and retain customers?

This question mostly applies to Crowley Properties. To attract customers to stay at our properties, we focus on quality and value.

If you look at any of the property links you will see that we have:

  • 5+ bedrooms: The more guests you can accommodate, the more the group can spread out the nightly cost ($1,000/night spread out over 10 guests is only $100/night — much cheaper than any quality hotel).
  • 3+ bathrooms: If you have 10+ guests, you need to have a lot of bathrooms.
  • Amazing outdoor and common areas: This is what grabs the customer and gets them excited.
  • Professional photos: Pictures are what books a place. Everything should be perfect in the pictures, otherwise retake them.
  • The details: Customer service, informative listings, and a spotless property are all essential.

How are you doing today and what does the future look like?

Business is good! Crowley Holdings and Crowley Properties are both profitable and growing. They more or less were always profitable from the jump.

Crowley Holdings will continue to grow organically. Currently, we operate around the country and have found a niche in sand and gravel supply contracts. In the future, I imagine  we will grow to have a real presence in New Orleans — and Louisiana at large — as a legitimate construction company. We are able to shake things up a bit by bringing in tricks, techniques, and technology that aren’t common in the construction industry. In five years, I anticipate  we can be a $50-100 million revenue business.

Crowley Properties continues to grow and be profitable. I am currently adding five to 10 units per year. We just started expanding into Tampa, Fla. We have two properties there, with a third in the works. I’m currently deciding if I should keep growing organically or whether I should go out and raise some cash and add 20-30+ units peryear. If anyone has advice here, I would love to hear it!

Crowley Hauling is a solid business. It will never be a hockey stick type of company. But it is a good way to diversify. I also could see pairing Crowley Hauling with Crowley Holdings. 

Ultimately, I believe we’ll be able to win big levee or construction projects in New Orleans and run our dump trucks on the job. This way, we can double dip. I can see us getting to 10 dump trucks in the next year or two. Beyond these goals, I’m not sure if I want to take it to the next level — 20, 30, 40 dump trucks. It’s doable, but we will see.

Did you ever have an “oh shit” moment where you thought it wouldn’t work?

Honestly, not with my three core businesses. However, I have launched products or businesses that did not work, including:

  • Playboy alarm clock app: My first product that I successfully launched to the app store. I spent around  $5,000 on it and made maybe $500 on it.

  • Down River Design: I took what I learned from the Playboy alarm clock app and launched a web and app development company. I built the alarm clock with a software development firm in India. So I did the same thing for clients. I made some money, but I could never turn the corner of getting enough business to hire or grow.

  • ZAP DRD: I partnered with the India-based company, Zaptech Solutions, giving it the name ZAP (Zaptech) DRD (Down River Design). I had the same problem. This move helped, but the business still never became super profitable.

  • Lead-Buddy: This lead generation business sort of worked but never turned the corner.

In addition to a few other ideas that never made it.

Through starting your businesses, have you learned anything particularly helpful or advantageous?

Your business will never be perfect. Often, you see people trying to make everything perfect before launching their business or product. Most businesses fail before they start because they never make it to market (I don’t have any stats to back this up, but I would be willing to wager it is correct). You need to get it out to market ASAP — asap and you can always tweak it. 

What platform/tools do you use for your business?

Trello: What we use to organize thoughts and projects. 

Clickup: Similar to Trello but with more automation features. I might move the Crowley Holdings team from Trello to Clickup. I have been pretty impressed with it. 

Slack: A must-have tool to communicate with the team efficiently. 

Macs: I was a longtime PC guy, but Apple finally won! Most of what I do is communicate with people. Being able to text and call from my computer helps out in a big way.

Virtual Champions: I think I’ve finally found a good virtual assistant. I’ve only used it for a short time, but I am already getting a lot of tasks out of backlog. 

What have been the most influential books, podcasts, or other resources?

The 4-Hour Workweek”: I read/listened to this book a few months ago, but I wish I had years ago. It all aligns well with my thinking: work smarter, not harder. Become efficient with your time. Use the free time this creates however you choose!

My First Million” podcast: You all know it 🙂

The Pitch” podcast: Slightly under the radar, it’s like the real “Shark Tank,” meaning the pitches are much closer to what it’s like in the real world. 

Advice for other entrepreneurs who want to get started or are just starting out?

I’ll come back to my mottos: Screw it — just do it. Let it rip! You need to get out there and do it. If the business fails — well, you can apply what you learned  to the next business. 

Ask for advice. It took me too long to do this. Business is not that complicated. There are plenty of people out there who have done it before, who have made those same mistakes. 

Also, most entrepreneurs  and business owners actually like talking about their business and giving advice. Myself included! So never be afraid to network and ask questions.

You don’t need to work as hard as people like Gary Vee say. You don’t need to grind 20 hours/day for your business to work. Yes, it might take longer for it to be successful if you don’t but that doesn’t mean it’s going to fail.

Delegate. You need to delegate to grow — your business will never scale if you can’t learn to do this.

Are you looking to hire for certain positions right now?

I would be interested in a right-hand man/woman — someone I could teach all of my businesses, and eventually, have them handle a lot of the day-to-day things I handle. I don't know how or where to find someone like that. As such, I haven’t advertised or looked for this role yet.

Where can we go to learn more?

Crowley Holdings

Crowley Hauling

The Syd 

Bulk Aggregate Supply

Personally, I find being the CEO of a startup to be downright exhilarating. But, as I'm sure you well know, it can also be a bit lonely and stressful at times, too.

Because, let's be honest, if you're the kind of person with the guts to actually launch and run a startup, then you can bet everyone will always be asking you a thousand questions, expecting you to have all the right answers -- all the time.

And that's okay! Navigating this kind of pressure is the job.

But what about all the difficult questions that you have as you reach each new level of growth and success? For tax questions, you have an accountant. For legal, your attorney. And for tech. your dev team.

This is where Hampton comes in.

Hampton's a private and highly vetted network for high-growth founders and CEOs.

See if you're a fit...

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